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The Woodland Realm was established by Oropher in S.A.750, a Sindarin lord of Doriath, after the War of Wrath.[3] Unlike most Sindar, Oropher and his household declined the Valar's offer to depart from Middle-earth for Valinor. Instead he migrated eastward and became the King of the Nandor of Greenwood the Great. The few Sindar who had come with him were soon merged with the Silvan Elves, adopting their customs and language and taking names of Silvan form and style.[4] Oropher and his household wished to return to a simple existence natural to the Elves before they had been disturbed by the Valar.[4]

Originally Oropher's realm encompassed the entirety of Greenwood, with its capital at Amon Lanc. However, during the Second Age, he and his people migrated north three times.[5] According to one tradition, the first movement was northward beyond the Gladden Fields, due to Oropher's desire to distance himself from the increasing encroachments of the Dwarves of Moria and his resentment of the intrusions of Celeborn and Galadriel in Lothlórien. However his people did maintain constant intercourse with their kin west of the Anduin.[4] Oropher was also disturbed by the reports of Sauron's rising power and by the end of the Second Age he dwelt in the western glens of the Emyn Duir or Dark Mountains and his people lived north of the Men-i-Naugrim or Dwarf-road.[5]

Oropher's son, Thranduil, succeeded him as king of the Woodland Realm[4] and ruled for the duration of the Third Age.

Around T.A.1050 an evil entity known as the Necromancer (later identified as Sauron) inhabited the abandoned halls of Amon Lanc, and Greenwood grew infested with Orcs and giant Spiders.[7] The Wood-elves retreated yet further north[4] and many landmarks were renamed: Greenwood became Mirkwood, the Emyn Duir the Mountains of Mirkwood or Emyn-nu-Fuin, and Amon Lanc was known as Dol Guldur, the Hill of Sorcery.

By the middle of the Third Age, the Silvan Elves of Mirkwood were much reduced in number though Mirkwood still had a greater population of Elves than Lindon, Rivendell, or Lothlórien.[8] To avoid the encroachment of the Necromancer from the south, they dwelt in the lands north of the Forest River, living mainly in and around the Elvenking's Halls. They also had become increasingly withdrawn and wary of strangers, though they did trade with the neighbouring realms of Erebor and Dale, and imported wine from Dorwinion via the River Running. The former traffic came to an end upon with the destruction of Erebor by the dragonSmaug in T.A.2770.[7]

In T.A.2941,[7] Thranduil's people were disturbed, three times, by a band of Dwarves while feasting in the forest. The Dwarves were captured after the third interruption and brought to the Elvenking's halls. Though they had trespassed, they were not imprisoned until after they had been questioned and refused to be forthright. Their leader, Thorin, refused to reveal the purpose of their journey from their halls far to the west in Eriador.[9] The others, taken separately, had been questioned, refused to speak openly, and also spoke insultingly of the Elves.[10]

Thranduil was content to wait for the Dwarves' stubborness to subside. Though prisoners in the king's dungeons, they were not ill-treated by the Wood-elves who "were reasonably well-behaved even to their worst enemies, when they captured them."[9] After many days of imprisonment, they escaped with the help of their companion, the hobbitBilbo Baggins, who had avoided capture using a magic ring.[10]

Sometime later, the Elves heard that Smaug, provoked by the escaped dwarves, had left Erebor to attack Lake-town where he was slain by Bard the Bowman. With that news, it was believed that the dwarves must have died and the wealth of Thror, augmented by Smaug's pillage of Dale, was left unprotected. Thranduil immediately assembled an army and marched towards Erebor. On the way, they met messengers from Bard seeking aid for the people of destroyed Lake-town. Thranduil being "the lord of a good and kindly people," turned his march to lend them aid.[11] He gave them a great store of goods and skilled Elves stayed to help the people erect shelters for the winter. He and Bard, a descendant of Girion of Dale, then joined forces and marched north in arms as Thranduil had perceived that the swift spreading news of Smaug's death was "an ill wind . . . that blows no one any good."[11]

On arriving, however, they found Thorin and his company alive, and Thorin, despite their early attempts to negotiate, refused to relinquish his claim on any of the treasure and had secured Erebor against an assault. Thranduil and Bard then lay siege to the Dwarves, who awaited aid from their relatives in the Iron Hills to the east.[12] Hoping to avert battle, Bilbo delivered the Arkenstone to the Wood-elves and Men, so they could use it to bargain with Thorin.[13] This act earned him great respect from the Elvenking who stated that he was "worthy to wear the armour of elf-princes," which referred to the mithril-mail shirt, found in the dragon's hoard, that Thorin had given him.

The next morning, Bard and Thranduil entered into negotiations with an angered Thorin, who agreed to pay one-fourteenth share of the treasure in exchange for the stone. Thranduil was reluctant to start a war over gold, but when the forces of Dáin arrived the next day, before the trade had been made for the Arkenstone, the Dwarves proceeded to attack. While the Elves, Men, and Dwarves skirmished, other enemies, who had learned of the dragon's fall, arrived. Orcs and Wargs from the Misty Mountains and Grey Mountains had joined forces to march to the Lonely Mountain and sieze the hoard. Under the council of Gandalf, Elves, Men, and Dwarves joined together against their common foes. In the ensuing Battle of Five Armies, many Wood-elves were slain, [14] as was Thorin Oakenshield, but afterwards an agreement was reached for the division of the dragon hoard.[15]

Sauron, now revealed as the evil presence which had abandoned (not, as it had been thought at the time, driven out of) Dol Guldur, from his rebuilt stronghold in Mordor sent three Nazgûl to reoccupy Dol Guldur in 2951.[7] On 20 June3018 a force of Orcs attacked the Woodland Realm from this base, the purpose of this raid being to provide a distraction and facilitate the escape of Gollum[17] who had been entrusted to Thranduil's care by the RangerAragorn.

During the Fourth Age the Woodland Realm prospered, free of enemies. A group of Wood-elves led by Legolas helped rebuild Minas Tirith and settled for a time in Ithilien.

The eventual fate of the Woodland Realm is unknown. In Fo.A.120 Legolas, having seen the sea during the War of the Ring, eventually sailed west to Valinor, reputedly with Gimli at his side.[19] Like all Elves the people of the Woodland Realm were destined to either leave Middle-earth for Valinor or to 'fade' and become rustic woodland spirits. Given Oropher's refusal to leave Middle-earth at the end of the First Age was rooted in a desire to 'live naturally' as Elves had before being contacted by the Valar, it seems likely that the latter was the fate of Thranduil and most of his people. However, the ultimate fate of the last Elvenking and the remaining Elves in the Fourth Age is unknown.